Upper Matecumbe Key Travel Guide

Tourist Guide

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.
A pier extending into calm waters with a covered seating area and a sandy beach.
A pelican standing on a wooden dock.
A pier with birds perched on poles, a sign, and a bridge in the background.
A calm lake with a reflection of trees and a cloudy sky.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is 4.440.982 ₫ per night from 9 Aug to 10 Aug
4.440.982 ₫
6.917.814 ₫ total
9 Aug - 10 Aug
includes taxes & fees
Stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their ...
9.2/10 Wonderful! (1,367 reviews)
"Clean room, great restaurants in the property. Staff is very friendly and a big shout out to the staff at the Cheeca Lodge Spa esthetician Milly and the front desk Robbeisha that made my relaxing spa experience very enjoyable."

Reviewed on 6 Aug 2026

Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is 3.969.292 ₫ per night from 11 Aug to 12 Aug
3.969.292 ₫
5.943.591 ₫ total
11 Aug - 12 Aug
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is 4.415.162 ₫ per night from 19 Aug to 20 Aug
4.415.162 ₫
6.888.109 ₫ total
19 Aug - 20 Aug
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
Amara Cay Resort
See all 2,772 properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (719 reviews)
"The room was conveniently equipped and smartly thought out so it worked very well. The only downside was occasionally noisy neighbors walking the hallway and talking, laughing loudly. If you value a clean environment, inside and out, you'll rate this resort highly. Parking next to the room, friendly ..."

Reviewed on 5 Aug 2026

Breezy Palms Resort
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this houseboat in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
9/10 Wonderful! (166 reviews)
"The houseboat were a great experience not only for the kid's but the adults also. Seeing the manatees swim around the cove was awesome! It was a great place to meet your neighbors as the porches are very close. The swimming pool is a great addition to the property! If going back to the area, I would ..."

Reviewed on 27 Jul 2026

Treasure Harbor
Island Bay Resort

Island Bay Resort

2.5 out of 5
92530 OVERSEAS HIGHWAY Tavernier FL
Stay at this beach aparthotel in Tavernier. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff in their reviews. Popular ...
10/10 Exceptional! (177 reviews)
"To us it was a slice of paradise. Able to snorkel, paddle board and kayak. It was peaceful, and just what we needed. Delana and Anna were so, so nice and sweet. We stayed in the Bahia cottage and space and decorations were perfect for us, online pics dont do it justice. Just 10 cottages, adults only. ..."

Reviewed on 4 Aug 2026

Island Bay Resort
See all properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Upper Matecumbe Key attractions

A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.
See properties